本篇論文利用不對稱催化的方式得到的化合物8a以及掌性雙烯雙醇化合物6當作起始物合成番荔枝科乙醯化合物( annonaceous acetogenins )中含有-相鄰兩個四氫呋喃 ( adjacent bis-tetrahydrofurans ) annonaceous acetogenins的中心結構的天然物Squamocin-M (1)，藉此發展具有相鄰兩個四氫呋喃的番荔枝科化合物之合成方法。本篇利用亞甲基繫繩以及環閉合置換反應建構其中心結構，之後利用交叉置換反應和末端具有離去機的長碳鏈，反應得到關鍵中間物。接下來預期使用末端炔類化合物10b做為親核試劑，以及官能基的轉換得到最終產物天然物Squamocin-M (1)。 To develop a new and efficient synthetic methodology for annonaceous acetogenins, a large family of nature product containing adjacent bis-tetrahydrofurans as the core structure, we chose the nature product Squamocin-M (1) as our target molecule and constructed the adjacent bis-tetrahydrofurans core by using chiral molecule 6 and 8a as starting material. Optical active 8a was generated from the corresponding meso diol by the asymmetric sparteine-copper (II) catalyzed esterification. Methylene acetal was used as the linker to connect diene 6 and mono-protected diene 8a, and then ring-closing-metathesis reaction was applied to provide the precursor of the adjacent bis-tetrahydrofurans structure. The cross-metathesis reaction was used to extend the carbon skeleton. We plan to apply alkylation reaction for the desymmetrization and accomplish the total synthesis of Squamocin-M.
